The Masters Real Estate Search

The Masters Properties for Sale

The Masters at Kaanapali Hillside is a picturesque, gated community that sprawls across 42 acres in Lahaina. Established in 1991, The Masters holds some of Kaanapali’s most notable and desirable real estate, as the community does not permit vacation rentals, and residents must own and occupy. Along with that unique form of privacy, The Masters also features amenities like two swimming pools, four tennis courts, and a location just minutes from Kaanapali Beach.

The Master real estate at Kaanapali presents homebuyers with a curated selection of properties from which to choose, encompassing the top of Kaanapali Royals Golf Course. The community is comprised of under 200 luxury condos that showcase maple, granite, and bamboo details. The Masters golf condos in Kaanapali are discoverable with between one and three contemporary layouts and unquantifiable commodities like tranquility and privacy. If you are interested in purchasing one of The Masters condos for sale in Kaanapali, please contact us today.

Our website features the best The Masters real estate search for homes, condo, land and foreclosure properties available. It is the only site you will ever need! It is easy-to-use and updated by the official REALTOR®’s database every 15 minutes. 

You can save searches, and get daily email alerts of new listings, price changes, sold data, and market reports. Our Interactive Map Search allows you to view properties on a map or refine your search by drawing the boundaries around the area you desire.

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Newest The Masters Properties for Sale

$1,680,000
2 Beds 2 Baths 410361 MLS ACTIVE Status Keala O Wailea BLDG.
Discover one of Wailea's rarest offerings ; a beautifully appointed ground-floor residence that pairs effortless access with exceptional views. This stunning 2-bedroom condominium at Keala O Wailea offers a combination seldom found: the convenience of single-level living, breathtaking ocean views, and the privacy of one of the community's most desirable locations. Thoughtfully positioned in a quiet corner of the complex, this meticulously maintained home enjoys an expansive green lawn just beyond the lanai, making it an ideal retreat for pet owners and those who appreciate seamless indoor-outdoor living. The sense of privacy is remarkable, creating a peaceful sanctuary surrounded by lush tropical landscaping. Inside, every detail reflects quality and care. High-end luxury furnishings, sophisticated finishes, and several custom enhancements elevate the home well beyond the ordinary. The spacious, open-concept floor plan is filled with natural light and captures the beauty of Wailea from the main living areas, creating an inviting atmosphere for both everyday living and entertaining. Keala O Wailea is one of Wailea's premier luxury residential communities, ideally perched above the Wailea Blue Golf Course. This gated enclave offers an exceptional island lifestyle with resort-inspired amenities, including an elegant pool and spa, a beautifully appointed pavilion with an outdoor kitchen, and a spacious fitness center. Just moments away are Wailea's world-renowned beaches, championship golf courses, luxury shopping, acclaimed restaurants, scenic coastal paths, and the unparalleled natural beauty that defines South Maui. Whether you're searching for a full-time residence or an elegant island retreat, this exceptional home embodies the privacy, comfort, and refined island lifestyle that make Wailea one of Hawaii's most coveted places to call home.

67 Wailea Gateway Pl Unit 6-103, Kihei

Listing courtesy of Hawaii Life (W).

$649,000
3 Beds 2 Baths 410350 MLS ACTIVE Status Villas At Kenolio I BLDG.
Welcome home to Villas at Kenolio 4A, a spacious 3-bedroom, 2-bath residence located just moments from the ocean and North Kihei’s beautiful nightly sunsets. This desirable residential community offers convenience at every turn, along with resort-style amenities rarely found in a residential complex, including an expansive swimming pool with a dedicated lap section, hot tub, fitness center, playground, and welcoming outdoor gathering areas. Unit 4A features a unique and flexible floor plan, with the third bedroom located in the upstairs loft. Create a private guest suite, comfortable home office, fitness area, or additional living space to suit your lifestyle. The home also offers two separate lanai areas, including a fully covered lanai off the kitchen and a second outdoor space near the front entrance. Stay comfortable year-round with central air conditioning, plus individual window AC units when you prefer to cool only certain areas of the home. Brand-new carpet was installed in July 2026, providing a fresh foundation for the next owner. Additional highlights include two assigned parking stalls and a pet-friendly community. Directly across the street, the newer Hilton Grand Vacations Maui Bay Villas has helped transform the surrounding area, creating an elevated resort-like atmosphere while still offering the ease and comfort of residential living. With convenient access to the ocean, beaches, shopping, dining, and everyday essentials, Villas at Kenolio 4A is an ideal home base for enjoying everything the Maui lifestyle has to offer.

40 Halili Ln Unit 4A, Kihei

Listing courtesy of Coldwell Banker Island Prop-Ku.

$1,399,000
1 Beds 2 Baths 410343 MLS ACTIVE Status Wailea Ekahi Iii BLDG.
Experience effortless island living in this beautifully remodeled Wailea Ekahi Village condo, one of Wailea's most sought-after beachfront communities. This rare and desirable 1-bedroom, 2-bath floor plan is ideally positioned to capture ocean and garden views, with both the living room and primary bedroom opening directly onto the spacious covered lanai. A comprehensive 2025 remodel features ceramic tile flooring, solid-core doors, granite countertops, stainless-steel appliances, and quality finishes throughout. Vaulted ceilings, abundant natural light, and seamless indoor-outdoor living create an inviting island retreat. Air conditioning throughout, ample storage, and two bathrooms with walk-in showers provide everyday comfort and convenience. Offered fully furnished and turnkey, this residence is ready to enjoy from day one. Wailea Ekahi Village spans 34 acres of meticulously maintained tropical grounds with direct access to world-famous Keawakapu Beach. Residents enjoy four swimming pools, a beachfront pavilion, BBQ areas, Pickleball courts and beautifully landscaped walking paths. Wailea Ekahi is a pet-friendly community. It is also one of the select Wailea condominium complexes eligible for the highly desirable Wailea Golf Club membership. Just minutes from championship golf, The Shops at Wailea, luxury resorts, fine dining, tennis, and some of Maui's most spectacular beaches, this exceptional property is perfectly suited as a primary residence, second home, or highly desirable vacation rental.

3300 Wailea Alanui Dr Unit 40E, Kihei

Listing courtesy of Romvari Realty Ltd.

$550,000
2 Beds 1 Baths 410339 MLS ACTIVE Status Pohailani Maui BLDG.
Recently Upgraded 2-bedroom Garden View Unit at Pohailani Maui Discover tranquility in this beautifully updated two-bedroom, one-bath garden-view condo at the serene Pohailani Maui. This inviting unit features a remodeled kitchen and bathroom, elegant tile flooring throughout, and the convenience of a full-sized washer and dryer. Set in a lush, tropical landscape, Pohailani is a low-density residential community designed for comfort and peace. Mature foliage creates a natural canopy that provides cool shade throughout the day, while gentle trade winds bring a refreshing breeze to keep the air comfortable and inviting. Relax or read on your spacious private lanai, a perfect spot to unwind and enjoy the garden views. This unit includes one assigned parking space and access to excellent amenities, including two large swimming pools, tennis courts, and barbecue areas. Located in breezy Kahana, just moments from the beach and a short walk or bike ride to nearby shops and restaurants, this unit offers the best of Maui living. Sold furnished (with some tenant exclusions), this is an ideal opportunity for those seeking a serene island lifestyle. Tenant occupied—48 hours’ notice required for showings. Lease runs until 9/30/26. Please contact your preferred real estate professional for more information.

4435 Lower Honoapiilani Rd Unit 142, Lahaina

Listing courtesy of Berkshire Hathaway Maui Prop-L.

$4,795,000
3 Beds 4 Baths 410334 MLS ACTIVE Status Papali Wailea BLDG.
Where do timeless design, ultimate privacy, and panoramic ocean vistas all converge in Wailea? Welcome to Papali #17. Perfectly positioned in the community’s premier location, this exquisite residence is being offered for the first time since the original developer release. This single-level three bedroom and three-and-a-half baths provides the comfort and presence of a private home with the carefree and secure lock and leave benefits of a luxury condominium lifestyle. Sweeping ocean and outer-island views are complemented by Papali’s award winning design, contemporary architecture, and distinctive copper rooflines. Set on over ten acres of beautifully maintained tropical landscaping, Papali offers an exclusive sense of serenity with only two homes per acre providing privacy, tranquility, and a spacious sense of place just moments from Wailea’s pristine beaches, golf, dining, and shopping. Inside highlights include soaring vaulted ceilings with Alaskan Yellow Cedar beams, rich African mahogany millwork, limestone flooring, and a gourmet kitchen with premium granite surfaces. Flooded with natural light, expansive glass doors, and open generous lanai spaces for seamless indoor-outdoor living. Perfect for sunset gatherings and relaxed island evenings under the stars. A private garage, abundant storage, and dual entry points complete this rare and remarkable offering - furnished for your turn-key Maui lifestyle. Papali #17 isn’t just a home – it’s a legacy. Wailea’s most extraordinary offering.

3100 Wailea Alanui Dr Unit 17, Kihei

Listing courtesy of Coldwell Banker Island Prop(S).

$4,500,000
2 Beds 2 Baths 410325 MLS ACTIVE Status
Laulea is often translated as “peace and friendship,” which feels particularly appropriate for one of Spreckelsville’s most desirable private roads. Set on just under one-third of an acre, this inviting house and cottage property captures the relaxed character of Maui’s North Shore. The two-bedroom, two-bath main home was completely rebuilt in 1996 with style, warmth, and distinctive details, including seashell relief work, bamboo accents, and ohia posts. Skylights, open-truss ceilings, and an open kitchen and living area fill the home with natural light, while two spacious covered lanais extend the living space outdoors and create inviting settings for dining, relaxing, and gathering with friends. Built in 2005, the elevated cottage has its own Balinese-inspired character, with merbau wood and travertine floors, vaulted ceilings, Venetian plaster, and thoughtful architectural touches throughout. A flexible bonus space below the cottage provides additional room for a home office, gym, studio, storage, or other uses. The lovely backyard and two outdoor showers are perfectly suited to life near the beach. Multiple beaches and surf spots are nearby, along with Maui Country Club, Kaunoa Senior Center, Pa?ia, and convenient access to OGG, Whole Foods, and Costco. Peaceful, private, and full of personality, this is a special little compound in one of the North Shore’s most sought-after neighborhoods.

450 Laulea Pl, Paia

Listing courtesy of The Maui Real Estate Team Inc.

$945,000
2 Beds 1 Baths 410324 MLS ACTIVE Status
Welcome to 420 Haumana Rd. An investor's dream located on Maui's North Shore. Set on six-plus lush acres in Haiku, this rare offering delivers land, ocean views and unlimited potential. Easy access down Haumana's paved road, a genuine rarity in Haiku where so many parcels sit at the end of rough gravel roads. Terraced areas, open spaces, interior roadways, and three separate driveways along Haumana Road that make every corner of the land easy to reach. At the heart of it all sits a permitted 860 square foot main home, two bedrooms and one bath, ready for a full renovation to bring it back to life. The grounds are abundant with mature, fruit-bearing trees, such as avocado, mango, banana, lilikoi, coconut, mandarin and star fruit. The property is supported by water catchment and county electric. A private well is also located on the property. Beyond the main home are multiple additional structures in varying condition, offered as-is and full of possibility for a buyer ready to reimagine them. Located close to the waterfalls and hiking trails that define this side of the island, yet private and quietly its own, this is a one-of-a-kind property perfect as a homestead, investment property, a working agricultural parcel, or a legacy estate shaped over the years. Opportunities like this do not come often. Call your favorite realtor today to schedule a showing! POF are required prior to all showings.

420 Haumana Rd, Haiku

Listing courtesy of Compass-W.

$650,000
410323 MLS ACTIVE Status
Welcome to Lot 11 at Maluhia Country Ranches, an extraordinary opportunity to create a legacy estate within one of Maui’s most exclusive gated country enclaves. Encompassing approximately 2.42 acres on the coveted ocean side of the community, this exceptional homesite offers a rare combination of breathtaking natural beauty, remarkable privacy, and an ideal canvas for a custom residence designed to embrace the island’s indoor-outdoor lifestyle. From first light to the golden hues of evening, the property is framed by sweeping vistas that capture the Pacific Ocean, Maui’s rugged North Shore, and the iconic slopes of Haleakala. Year-round sunrises paint the landscape with remarkable color, creating a spectacular backdrop that evolves with every season. What truly distinguishes this offering is its expansive, naturally level building area—a rarity among large acreage homesites on Maui. The thoughtful topography provides the opportunity to design a residence where living spaces transition effortlessly onto broad, manicured lawns, resort-inspired outdoor entertaining areas, and a private pool, all without the significant grading and site work often required on comparable parcels. The result is greater design flexibility, enhanced livability, and the potential for substantial savings during development. Agricultural zoning further enhances the property’s versatility, allowing for a primary residence and an accessory dwelling, subject to county regulations. Whether envisioned as a private family retreat, an elegant multigenerational estate, or a refined island sanctuary for generations to come, Lot 11 provides the setting to bring that vision to life. Perched at one of the community’s most desirable elevations, the property enjoys a climate that many consider among Maui’s finest—offering warm, sunny days tempered by refreshing trade winds. Here, you’ll experience the perfect balance between the cooler elevations of Upcountry and the warmer coastal climates of West and South Maui, making outdoor living enjoyable throughout the year. Maluhia Country Ranches is a boutique gated community of just 51 estate parcels, thoughtfully planned to preserve the area’s rural character while offering modern conveniences. Beyond its beautifully landscaped entrance lies a peaceful setting where custom homes are thoughtfully positioned to maximize privacy, views, and the surrounding natural beauty. Despite its tranquil atmosphere, the community is conveniently located approximately 30 minutes from Central Maui’s shopping, dining, and everyday amenities, including Costco and Whole Foods, while Kahului Airport is just a short drive away. Essential infrastructure is already in place, including underground utilities, a private water system, high-speed internet availability, and weekly refuse service. Adding even greater value, the seller will include completed septic plans, a topographical survey, and a geotechnical report—important resources that can help streamline the planning and permitting process, allowing you to focus on creating a residence uniquely tailored to your vision. Rarely does a homesite offer this harmonious blend of expansive usable land, commanding ocean and mountain views, exceptional privacy, and effortless buildability. Lot 11 at Maluhia Country Ranches is more than vacant land—it is an invitation to create an extraordinary Maui estate where timeless architecture, natural beauty, and island living converge.

21 Lahaole Pl Unit 11, Wailuku

Listing courtesy of Berkshire Hathaway Maui Prop-L.

$29,900,000
5 Beds 6 Baths 407766 MLS ACTIVE Status
Perched on one of Makena’s most coveted cliffside locations, this contemporary direct-oceanfront estate is perfectly situated along an intimate cove, offering breathtaking, unobstructed Pacific views from nearly every room. Set on over 22,190 sq. ft. of land, this two-story, five-bedroom, five-and-a-half–bath residence is a masterpiece of luxury and Hawaii’s signature indoor–outdoor living. Designed by world-renowned architect Guy Dreier, the home is a livable work of art, featuring soaring ceilings, dramatic architectural lines, and an innovative floor plan. Step through the entryway into an entertainer’s paradise. The expansive great room flows effortlessly through large pocket doors to the oceanfront deck, where a stunning infinity-edge pool appears to spill into the sea—ideal for sunset gatherings or peaceful mornings with coffee in hand. Multiple living and dining areas, along with a dedicated service area, create an unparalleled setting for both intimate dinners and large-scale celebrations. The exquisite primary suite and three guest suites each offer private ocean-view lanais, providing serene retreats with panoramic vistas. A beautifully appointed attached Ohana unit adds exceptional flexibility for guests, extended family, or a caretaker. Move-in ready and designed for effortless hospitality, this is more than a home—it’s a true Makena masterpiece blending modern coastal luxury with the timeless beauty of Maui’s south shore.

5050 Makena Rd, Kihei

Listing courtesy of Discovery Makena Realty LLC.

$669,000
2 Beds 2 Baths 410317 MLS ACTIVE Status Kihei Garden Estates BLDG.
Escape to island living at Kihei Garden Estates! This beautifully appointed 2-bed/2-bath loft-style condo sits just across the street from Waiohuli Beach in the heart of Kihei. Wake up to peaceful views of Haleakala and the ocean from your expanded lanai. Sold fully furnished, C-209 is turn-key ready for immediate enjoyment as a personal retreat, second home, or a popular vacation rental. The open loft-style primary suite features a king bed and en-suite bathroom with a large walk-in shower, while the second bedroom below offers a twin and double bed — comfortably sleeping up to six with the queen sleeper sofa in the living room. A split-system A/C keeps your condo comfortably cool, and the gourmet kitchen has been upgraded with modern appliances, ready for home-cooked island meals or entertaining on the lanai. Enjoy resort-style amenities including a heated pool, oversized hot tub, and a BBQ pavilion with outdoor kitchen — all set on the lush, tropical grounds of this 8-building, 84-unit boutique complex. Location is everything here: Times Market, shopping, banking, medical services, and some of Kihei's best "ONO"-rated restaurants are all close by, in addition to Waiohuli Beach and Maui's legendary sunsets. Don't miss your chance to own a piece of paradise — schedule your private showing today!

1299 Uluniu Rd Unit C-209, Kihei

Listing courtesy of Keller Williams Realty Maui-L.

$839,000
4 Beds 3 Baths 410310 MLS ACTIVE Status
Where Potential Meets Pa'ina! This Hali'imaile property is currently situated as a single-story, 3-bedroom, 1.5-bath main home plus a 1-bedroom, 1-bath studio — 4 bedrooms and 2.5 baths total, split across two living spaces(and may have nonconformities, Buyers to do their due diligence.) Ideal for multigenerational living, rental income, or simply extra room to grow into. The original aluminum roof nods to the home's plantation-era roots, while the interior has been renovated and well maintained over the years — tile, vinyl & laminate bamboo flooring, updated cabinetry, granite counters, and an open kitchen-to-dining flow. This home wears its age honestly and needs some TLC, but the bones are solid and the potential is real. Outside, a covered carport leads to a shaded, plant-filled patio, and a deck off the back opens onto a spacious yard framed by banana trees & more. From a few spots around the home, you'll catch genuine peek-a-boo ocean views — a rare bonus at this price point. A neighborhood park sits just around the corner. The biggest opportunity: the lot is zoned R-1 Residential with Urban zoning, opening the door to build up to 2 additional accessory dwelling units (buyer to verify all zoning/ADU potential with the County). 27 Paina Street is an honest home with good bones and real upside, ready for an owner to bring it to its full potential. The property is currently tenant-occupied. Do not disturb tenants. Contact your go-to Realtor for more info today! The Owner is a licensed Realtor in the State of Hawai'i.

27 Paina St, Makawao

Listing courtesy of Real Broker.

$619,900
1 Beds 2 Baths 410265 MLS ACTIVE Status Maui Kamaole BLDG.
COMING SOON •BEST PRICED MAUI KAMAOLE• This Unit K-105 is currently being NEWLY RENOVATED and will be available for showings in approximately 3 weeks once the listing becomes Active. 849 SQ FT 1 bed, 2 full bathrooms built in 1999 and renovated in 2026. Fresh Sherwin-Williams Pure White interior paint, BRAND NEW Sputnik dining chandelier, NEW recessed lights, newer cabinets with fully adjustable shelves, melamine interiors and under cabinet lighting. NEW Brushed nickel cabinet and door hardware throughout. Newer stainless steel refrigerator, dishwasher, microwave, and hot water heater. BRAND NEW vinyl plank floors in living room and bedroom. Professionally cleaned tile floors. Newer drapes throughout. 2 full bathrooms, 2 AC units 2 outdoor spaces! Great storage with freshly painted louvered doors and NEW brushed nickel door knobs and pulls! 3 closets in bedroom, ensuite bathroom with two sinks, counter to ceiling mirror, CLEAN shower over tub with tile surround. Furniture and recreation equipment included. BRAND NEW Queen Sofa Sleeper. Second bathroom has tiled shower and counter to ceiling mirror. 1 deeded parking space. Maui Kamaole is the NICEST, NEWER LOW-RISE Complex in a QUIET South Kihei LOCATION bordering Wailea across from the Kihei Boat Ramp and Kamaole Beach Park III. Complex amenities feature: 2 tennis courts, 2 pool spa pavilions, several Weber BBQ areas and gazebos with plenty of tables and chairs. This unit is a GREAT BUY so Please Standby to view the property once it becomes Active. Thank you for your patience!

2777 S Kihei Rd Unit K-105, Kihei

Listing courtesy of Coldwell Banker Island Prop(S).

$1,450,000
4 Beds 3 Baths 410224 MLS ACTIVE Status
Located in the heart of Central Maui, this thoughtfully updated 4-bedroom, 3-bath residence offers 2,155 sq. ft. of interior living space on a level 9,493 sq. ft. R-3 zoned lot. The back yard is fully graded and construction-ready for the next ADU. Renovated over the years of ownership and most recently in 2020, the home features an easy access primary bedroom, 18 panel fully-owned photovoltaic system, spacious garage with storage, and split A/C units throughout for added comfort. Interior highlights include a flex-use studio, dining area, family room, practical kitchen with stainless vent to roof, range, and refrigerator, while the exterior provides the washroom with washer and dryer and additional storage room. With elegant bamboo and laminate flooring, concrete slab construction, asphalt composition shingle roofing, and all county utilities, the property offers a well-balanced blend of function and comfort. Its flexible layout makes it well suited for extended living, an adult care home operator, child daycare space, or a home with maid’s quarters. Conveniently situated near the airport, shopping, schools, medical services, and the many amenities of central Maui, this location offers everyday ease and accessibility while remaining close to the island’s business and transportation hub. Schedule your appointment for a showing today! VA Financing Available with low interest rate!

396 Kahiki St, Kahului

Listing courtesy of Compass-W.

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